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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2008 - Issue 1
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Original Articles

Three-Component Reaction of Triphenylphosphine, Dimethyl Acetylenedicarboxylate, and Aldehyde Benzoylhydrazones: An Efficient One-Pot Synthesis of Stable Phosphorus Ylides

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Pages 132-138 | Received 13 Dec 2008, Published online: 15 Feb 2011
 

Abstract

Protonation of the reactive 1:1 intermediate produced in the reaction between dimethyl acetylenedicarboxylate and triphenylphosphine by benzoylhydrazones leads to vinylphosphonium salts, which undergo Michael addition with the conjugate base of the NH acid to produce highly fanctionalized, salt-free phosphorus ylides in excellent yields.

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